title: Anthracene capped isobenzofuran: a synthon for the preparations of iptycenes and iptycene quinones.
abstract: Anthracene capped isobenzofuran 5 (5,6-(9,10-dihydroanthracen-9,10-yl)isobenzofuran) was synthesized for the first time. It is a highly reactive and versatile synthon for the synthesis of iptycene derivatives via Diels-Alder reactions. Cycloadducts 10 could be readily deoxygenated to iptycenes 11. Two new reactions of PhI(OAc)(2)/TfOH have been explored. Endoxides 10 were directly oxidized to iptycene quinones 12, and isobenzofuran 5 was conveniently converted to triptycene dialdehyde 16. H-shaped centrally extended pentiptycene quinones 13 and 14 were also synthesized.
authors.affiliation: Department of Chemistry and Centre for Advanced Luminescence Materials, Hong Kong Baptist University, Kowloon, Hong Kong SAR, China.
authors.forename: Bao-Jian
authors.initials: BJ
authors.lastname: Pei
authors.forename: Wing-Hong
authors.initials: WH
authors.lastname: Chan
authors.forename: Albert W M
authors.initials: AW
authors.lastname: Lee